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The main messages that the audience gets from most of Willy Loman's actions can be summarized in the following:
This is because, as it is evident throughout the play, Willy Loman has never really had a backbone that would provide him with the self-assurance that is so needed to make good choices and move on through life. Part of this lack of back-bone comes from the fact that Willy was abandoned by his father so early in life. Also, right as he is left with his elder brother as his main keeper, his brother also leaves. Willy never really had the male role model that he very much needed to understand his role as a son, a father, and a husband. This is the main reason why he basically failed at all three.
The result of a living without guidance leads Willy to double-guess himself all of the time. On one hand, he calls himself "vital" and "well-liked" while, on the other hand, he has to ask his mistress whether he is funny, or whether he is likable. Likewise, while he feels sure that he is ready to go explore Alaska with his brother, he again double-guesses himself and asks Linda what she thinks about the possibility. Willy just is not capable of making an educated decision and create viable choices from them. He simply has no clue who he is, or what he has to offer.
Then there is the Chevy. When the car was first purchased it was a sign of great times to come. The car was one of Willy's prized possessions, and having come to own it represented a sign that his American Dream was well on its way to come true.
However, time has passed, and the Chevy no longer does the job it once did; like Willy, the car is outdated and needs a lot of fixing up. Yet, despite of all this, the mixed emotions that Willy has about it shows Willy's own inability to think objectively- he simply goes with what he feels at the time. This huge flaw is what leads his life on a road to nowhere.
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